Airport streaming - disappointing SQ so far

I'm intrigued with the idea of sitting in my chair using my iPhone to control iTunes as it streams CDs I've ripped as AIFF files to a highly portable 1TB USB hard drive directly connected to an Airport Extreme Base Station that functions as an NAS. At the moment, I'm listening to Infinity Quantum 2s being driven by a '70s vintage Concept receiver. I have a MacBook Air connected to the receiver via the headphone jack to RCA aux inputs on the receiver. The MacBook is receiving its signal wirelessly from the Airport Extreme with attached HD (where the iTunes Library is physically located). It is very cool to see my iTunes library and control it via iPhone. Unfortunately, the sound quality is only OK for non-critical background listening in my opinion. Sound is rather thin compared to the original CDs. I'm assuming a DAC would help somewhat. I've also read about using the output from an Airport Express connected directly to the receiver's RCA inputs. Some say this would be an improvement. Alternatively, the Airport Express could connect to a DAC and then the receiver. Any thoughts, suggestions, actual experience with something like this setup? I know I can get a used Airport Express for under $50. Hard to know how much one needs to spend on a DAC.

What bit rate are you using? I rip CDs to Apple Lossless format and they sound very good.
Full signal path is iTunes on my old macPro to Airport Extreme (Tower style) then via Wifi to Airport Express to DAC to Jolida Tube Amp to ALTEC speakers
(Or Von Scheweikert VR-4s). Control is done using iPhone 6S+ and the "Remote" app.

I use an old Audio Alchemy DAC since I can tie the Airport via Opticxal cable from the "headphone" jack, and run another out from my Oppo DV981HD disc player into the DAC via the composite port. Plus the Audio Alchemy DAC also does HDCD decoding.

I think your weak link is the analog out from the MacBook Air. My experience is that the robustness of the analog circuit after the digital conversion is the limiting factor for most portable devices. To get good battery life with light weight, Apple made many compromises. I would not doubt that the built-in DAC in the MBA is of less-than-stellar quality. I have two MBAs and several Mac Pros. I would not use the headphone jack on the MBA for anything other than headphones when traveling. If you have a spare headphone amp, you may want to put it between your MBA headphone jack and your receiver line input. The headphone amp would likely better drive your receiver than the raw headphone output of the MBA. I am very satisfied with the analog sound from my Mac Pro. I run it through a headphone amp and it sounds great. The MP is a true workhorse with some good stuff in it.

I suggest using an external DAC connected to the MacBook Air. Or get an Airport Express or Chromecast Audio to connect to your receiver. A CCA would be your lowest cost solution and it works well. I use both Airport Expresses and Chromecast to transfer music wirelessly to my various systems. I have no trouble using either from my iPhone or my Macs.

I think your weak link is the analog out from the MacBook Air. My experience is that the robustness of the analog circuit after the digital conversion is the limiting factor for most portable devices. To get good battery life with light weight, Apple made many compromises. I would not doubt that the built-in DAC in the MBA is of less-than-stellar quality. I have two MBAs and several Mac Pros. I would not use the headphone jack on the MBA for anything other than headphones when traveling. If you have a spare headphone amp, you may want to put it between your MBA headphone jack and your receiver line input. The headphone amp would likely better drive your receiver than the raw headphone output of the MBA. I am very satisfied with the analog sound from my Mac Pro. I run it through a headphone amp and it sounds great. The MP is a true workhorse with some good stuff in it.

I suggest using an external DAC connected to the MacBook Air. Or get an Airport Express or Chromecast Audio to connect to your receiver. A CCA would be your lowest cost solution and it works well. I use both Airport Expresses and Chromecast to transfer music wirelessly to my various systems. I have no trouble using either from my iPhone or my Macs.

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I suspect you are correct about the line out from the MBA. I ordered an Airport Express yesterday. Will try that first. Used ones are easy to find for around $30 or so. Thinking there may be a DAC in my future, but really confused about how much is enough after spending hours reading reviews.

Some say the DAC built into the Airport Express is good enough, due to the 16-bit/44.1KHz limit. Which is also what your AIFF files are. I've been using a number of Airport Expresses for several years, with and without, external DACs, with both an ancient Mac Mini and a Windows 10 laptop for storing the files, all AIFF ripped from original CDs.

I personally think the Airport Express optical out into a Schiit Modi 2 Uber sounds great. Avoid the Cambridge Audio DacMagic 100. It doesn't play nice with the Airport Express. Cambridge Audio blames the Airport Express (says it puts out too much jitter, which the DacMagic 100 can't handle). Regardless who is to blame, the combo is completely unusable. I've never had a problem with the Modi 2 Uber, plus it's affordable and a great sounding DAC.

many Mac laptops Do have a headphone jack with a combined Optical port built in. Not sure if the macBook Air has it. My wife's macBook does.
Anyway, if it does, (look for a red glow in the headphone jack!) you could connect an optical cable and a cheap DAC for better sound than your headphone to RCA cable gave you ...

I have 2 Airport Expresses in the house for AirPlay, one I go optical out to the Wolfson DAC in my Onkyo A-9010 integrated amp. The other I use with my vintage system, that one I use the DAC built in the Airport express. Both sound good to me, especially if I stream from my iMac that has the files downloaded to it. If I use my iPhone to stream to it with streaming Apple Music, it doesn't sound as good to me.